Joining the fray, Hiccup was acutely aware of just how cramped the canyon was. With steep, rocky slopes behind him and a two-ton iron train blocking his path forward, he felt really and truly trapped.

On the far rim of the canyon, he could see uniformed men taking up positions. More men sat on horseback, ready to chase down any Grimborn who attempted to flee. At his back, Viggo had abandoned his position on Skrill for a more compact, tactical position behind a boulder. Calculated, even amidst the chaos, Viggo ensured that each shot from his rifle counted.

To Hiccup's side, the twins were frantically digging through Barf and Belch's saddlebags.

"Ruff! Tuff!" Hiccup called, "What are you planning?"

The twins turned to face hiccup, grinning at him with wide, toothy smiles. Their arms were overflowing with dynamite.

"Thorston Surprise!" Tuffnut said.

"I get to be the one to throw the dynamite!" Ruffnut added.

"No, you did it last time. I want to be the one to blow up!"

"You always mess it up, Butt-Elf!"

Even with bullets hitting the ground at their feet, the twins were bickering and bashing heads. Hiccup groaned loud enough to put an end to their antics. They looked at him expectantly.

"We don't have time for this. We need to get everybody out of the canyon and into cover."

"We can do that!" Ruffnut volunteered.

"Yeah, we're on it, H!" Tuff said with a mock-salute.

Hiccup moved up, out of the potential blast radius, keeping his eyes on the slopes above him. Finding a vantage point, Hiccup fired six shots into the Flyers. Five hit their marks, and three agents fell to the ground. The remaining two slumped forward on their mounts, but Hiccup knew they wouldn't recover.

Inside the train cars, the passengers were growing emboldened. The presence of government agents inspired many of the once-beaten guards to rise up and reclaim their train. Charging from the train in droves, the Grimborn Gang was suddenly very outnumbered.

Two train cars up, Hiccup could see Hamish and Savage firing rounds into the ranks of guards, but it did little to deter the guards from charging at Hiccup. Backed against the train, Hiccup reloaded his revolver. He fired one shot into a guard's side before he was tackled by three more. Overwhelmed by their numbers and enclosed as he was, Hiccup was quickly subdued.

Knocked to the ground by the butt of a shotgun, his skull cracked against the rocky ground. His vision turned white and stars danced in his eyes. Defenseless, he clumsily threw up his arms to defend off the men's blows. They kicked at his ribs and head until Hiccup couldn't breathe and he was sure he would black out.

Three shots exploded above him and he was buried beneath the weight of the men.

"Come on, Hiccup! We don't have all day!" Snotlout complained. Pulling Hiccup from the pile of bodies, Snotlout thrust Hiccup's revolver into his hands and put his hat back on his head. "You really should be more careful. I can't constantly be saving you."

Hiccup swayed, reaching out for the stockier man's arm to steady himself. "Thanks, Snot. I owe you."

"Yeah, yeah." Snotlout waived him off, then whistled for Hookfang. "Just don't forget to tell everybody about how I so bravely rescued you from the clutches of death. "

Rolling his eyes, Hiccup whistled for Toothless. At the far end of the canyon, Hiccup could see the familiar shape cantering toward him.

"Sure, Snotlout. I'll be sure to tell everyone how you jumped the train, stopped it single-handedly, and still found the time to save my life."

"You would really do that for me?"

"No. Of course not." Hiccup snarked, bending his knees and preparing to jump onto his horse. Toothless flashed by and Hiccup grabbed hold of the saddle, using the momentum to pull himself up. The maneuver made his stomach roll and his ribs throb.

Toothless raced up the rocky slope, each thud of his heavy hooves jarring Hiccup's battered body. Hiccup pulled Toothless to a stop, joining the semi-circle that hard formed around Viggo. Then he slumped forward against Toothless's neck, breathing hard. Hamish, Sven, and Savage stood guard and offered the gang cover fire as they attempted to regroup.

"What's the plan, Viggo?" Heather asked.

"We need to take what we've found and leave," Johann said.

Viggo, atop Skrill, pursed his lips and looked out on the battlefield. "We will ride together until we hit the tree line. Then you are to disperse and disappear. Regroup in two days at Raven Point. Do not allow yourself to be followed."

"Wait, wait!" Hiccup interjected. "Where are the twin—"

As if on cue, an explosion rocked the canyon and shook the ground beneath their feet. Smoke and dust clouded the air, but just beyond, Hiccup could see the damage the twins had ravaged. The far ledge was gone; destroyed. Men and horses alike had been swept up in the ensuing landslide and were now pinned against the train.

"Found them." Snotlout said, throwing a thumb over his shoulder.

From the smoke, Barf and Belch emerged, their hides covered in thick, black soot. Atop their backs rode the twins, laughing and high-fiving as they charged past.

Exasperated with their methods, but undeniably pleased with the results, Viggo snapped Skrill's reins, pushing his horse into a gallop. Hiccup followed at his side, one hand gripping the saddle horn, and the other heavy with the weight of his revolver. The jolt of Toothless's gait was making him sick, but he pushed the horse onward. The tree line was in sight, and Hiccup was about to peel off from the group into the safety of the forest when Heather's scream ripped through the night.

Yards behind them, a single Flyer had pursued the gang in their retreat. Windshear, Heather's mount, was panicking. Rearing on her back legs and bucking forward, the horse threw her rider to the ground. A trained horsewoman, Heather should have tucked and rolled to soften the landing. She should have jumped back to her feet and calmed her horse. But she didn't. She was curled up on the ground, clutching at her shoulder and cursing. Dark, red blood spilled into the dirt, staining her fingers and the grey lace of her bodice.

"Snotlout, with me!" Hiccup shouted, pushing his own pain down and urging Toothless to reach her before the Flyer could finish the job. Raising his revolver, Hiccup closed one eye and shot the Flyer from his saddle.

Halting in front of Windshear, Hiccup vaulted from the saddle and attempted to calm the mare while Snotlout worked on pulling Heather from the ground.

"Oh, Thor, Fish is so gonna kill us!" Snotlout whined.

Heather was tucked into the boy's arms like a bride, but she looked nothing short of miserable. Hair clung to her sweat-covered forehead and she lolled her head against Snotlout's shoulder.

"Just get me home to him, first." She said weakly.

With Windshear calm, Hiccup tied her to Hookfang. Then, he helped Heather onto the mustang's saddle. He placed a hand on Snotlout's arm, "Get her to camp. No detours. Straight back to camp, Flyers be damned. Understand?"

"Yeah, yeah. I can do that. Right." Snotlout muttered, his face scrunched in a rare look of determination. "Okay, Hooky, get us home! Go!" He shouted spurring them forward. Hiccup watched as they disappeared into the tree line and hoped he had been quick enough.

xXx

Toothless carried Hiccup across the state until trees turned to desert and Hati had chased the moon across the long, arcing sky. Dawn was on the verge of waking when he finally urged Toothless to slow. If they didn't rest soon, Hiccup was certain he would keel over.

Nearing a familiar camping spot, Hiccup climbed down from the saddle and clucked his tongue for Toothless to follow.

The pair walked up a narrow path built into the side of a large rock formation. At the end, stood an erosional fin Hiccup had fondly dubbed The Dragon's Jaws because of the unique way the mouth of the cave protruded from the larger rock formation. The cave was high off the ground, giving Hiccup the ability to see for miles in any direction, and sharp rocks jutted up and down the mouth of the cave, serving as teeth for the dragon and acting as cover for Hiccup. Leading Toothless up the path, Hiccup was surprised to find the familiar shape of Skrill hitched to a tooth.

Viggo had erected a small camp in the mouth of the dragon. He was asleep on his bedroll, his back turned toward Hiccup. The remnants of a fire simmered softly in front of him. Hitching Toothless beside Skrill, Hiccup removed his bedroll from the saddle and stepped into the camp.

Immediately, Hiccup regretted the decision. Ever the light sleeper, Viggo was suddenly on his feet, his pistol level with Hiccup's eye.

"It's just me, Viggo." Hiccup said softly.

"I told you to disperse. Not follow me like a dog."

Insult aside, Viggo sat down and motioned for Hiccup to do the same. The man had removed his boots, overcoat, and vest, but he still looked more nouveau riche than outlaw. Anger flashed through Hiccup. Viggo wasn't bloodied or bruised. Unlike Hiccup, his clothes were not soiled with dirt or Flyer's blood. It wasn't right.

Hiccup exhaled.

That wasn't fair. Viggo had fought in the mud with the rest of them plenty of times. Viggo just…wasn't the kind of man to rush into situations. He fought with his mind, not his muscles. And although Hiccup was not particularly muscular, he was light on his feet and the only thing quicker than his trigger finger was his intellect. It was a dangerous skill set that Viggo had come to rely on. Somewhere, over the years, Hiccup had moved from skinny burden to Viggo's right-hand man. Viggo entrusted him to ensure his plans were carried out successfully. That's why he was the one in the line of fire. Because Viggo trusted him to make it out unburned.

Hiccup unrolled his bedroll and settled across from Viggo.

"It's not my fault that some old man stole my camping spot."

Viggo gave a short laugh at Hiccup's jab. "Like minds and whatnot, my boy."

Hiccup hummed a response and set to work on removing his boot, then his jacket, and finally, his prosthetic. Unlocking the latches, the metal base slid off first. Then, he pulled the sweat and blood-soaked sock from his stump. Setting the pieces beside him, Hiccup began to slowly massage the painful knots that had taken root in his remaining calf muscles.

"Heather was shot."

"I saw," Viggo said. "I also saw you rush to her defense. I trust she is safe?"

"As safe as one is with Snotlout. I had him take her back to camp for medical care."

Instead of lecturing Hiccup on the importance of field medicine or criticizing him for potentially allowing the Flyers to find their hideout as Hiccup expected, Viggo praised him.

"It was very brave of you to turn back for her."

"She would have done it for me." Hiccup replied.

"Yes, I'm sure she would. You've managed to inspire loyalty amongst outlaws. A difficult task, my boy."

"We're family." Hiccup defended.

"Nonetheless, you did well. I knew I could put my faith in you."

"I just did what needed to be done." Hiccup said, shrugging off the compliment. Robbing and killing innocent men were not activities that Hiccup took pride in. The boy rubbed his hands over a particularly sore knot and sucked in air through his teeth.

"Does it hurt?"

"My leg?" Hiccup frowned, wondering how much to tell the man. If he were being honest, his entire body felt like it had been hit by that train. His leg often hurt him after a day of riding and robbing, but the pain in his head and ribs exasperated everything. But he couldn't tell Viggo about it. Not when Viggo counted on him and needed him to be at his side to protect and encourage the gang. He couldn't have Viggo seeing him as weak or a burden on the gang.

"It's nothing. I just…landed wrong when I jumped the train. I'll be fine in the morning."

"Hiccup, you look like shit. And you've never been a particularly good liar."

"Blame my teacher." Hiccup snarked, but he supposed Viggo had a point. His hands were still black from his topple in the coal box, and he figured his face was an ugly mixture of black soot, blue and yellow bruises, and red blood. "Besides, " he started, "We can't all stay on the hill 'running point'".

Easing the pain enough to ignore the dull throbbing, Hiccup reattached his prosthetic. Typically, he would never sleep in the uncomfortable contraption. But here, in the wild with Flyers breathing down his neck, he couldn't afford to sacrifice security for comfort. He made to stand, Toothless still needed to be rubbed down and someone needed to take the first watch.

Viggo raised a hand to stop him.

"Sleep, son," Viggo said. "It's true that you took the brunt of tonight's excitement while I was merely an overseer. I can take first watch."

"No, no." Hiccup grunted, rising to his knees, "Toothless's leg will be hurting too. I need to check on him."

"I will tend to your horse. Rest."

Viggo's voice was uncharacteristically soft and Hiccup's bones were heavy, so he accepted the offer with little resistance. Using his jacket as a pillow, Hiccup curled toward the dying embers of the fire. Viggo had watched over him for over a decade, and he trusted Viggo to keep watch over them now. Here, in the mouth of the dragon and under Viggo's eye, Hiccup slept.